1. Field of the Invention
This invention relates to a process for preparing substituted oxatriazoles from the reaction of an oxime with an azo compound. This invention also relates to the production of certain addition compounds from the reaction of an oxatriazole with an azo compound.
2. Description of the Prior Art
Grundman, "Synthesis of Heterocyclic Compounds with the Aid of Nitrile Oxides," Synthesis, II, 344 (1970), surveys known methods of preparing substituted 5-membered heterocycles, e.g., oxatriazoles, via a nitrile oxide (--C.tbd.N.sup..sym. --O.sup..crclbar.) intermediate. These are two-step methods comprising first oxidizing an oxime to a halogenated species, e.g., hydroximic acid chlorides, and second dehydrohalogenating the halogenated species in the presence of an unsaturated compound, e.g., an azo compound. The dehydrohalogenating of the halogenated species generates a nitrile oxide which then condenses with the available unsaturated compound in a 1,3-dipolar cycloaddition. While many variations on each step are known, a convenient one-step process has yet to be reported. Grundman, supra, is here incorporated by reference.